105643-18-3

Upstream product

• 23204-80-0 (E)-1-chloro-2-(prop-1-en-1-yl)benzene 
• 64-19-7 acetic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 58824-53-6 1-(3-chlorophenyl)prop-2-en-1-ol 
• 108-24-7 acetic anhydride 

Downstream Products

• 1562996-42-2 (S)-1-(1-(3-chlorophenyl)allyl)-4-phenylpiperazine 
• 1562996-41-1 (S)-1-(1-(3-chlorophenyl)allyl)piperidine 
• 119125-31-4 (E)-3-(3-chlorophenyl)prop-2-en-1-ol 
• 770-23-0 (E)-3-(3-chlorophenyl)propenal 

Relevant academic research and scientific papers

Kinetic Resolution of Racemic and Branched Monosubstituted Allylic Acetates by a Ruthenium-Catalyzed Regioselective Allylic Etherification

We demonstrated the kinetic resolution of racemic and branched monosubstituted allylic acetates by a ruthenium-catalyzed regioselective allylic etherification. The reaction was effectively catalyzed by the chiral ruthenium catalyst, which was generated by [RuCl2(p-cymene)]2 and (S,S)-iPr-pybox and a catalytic amount of TFA, and both the allylic etherification product and recovered allylic acetate were obtained as an enantiomerically enriched form with up to a 103 s value.

Palladium(II)-catalysed Rearrangements of Allylic Acetates in the Syntheses of Methyl (10E,12Z)-9-Hydroxyoctadeca-10,12-dienoate (α-Dimorphecolate) and (2E,4Z)-Deca-2,4-dienal

Preparatively useful examples of the kinetically controlled PdII-catalysed rearrangement of (1E,4Z)-3-acetoxy-1,4-dienes into (2E,4Z)-1-acetoxy-2,4-dienes are described.These include the conversion of (2E,5Z,8Z)-4-acetoxydeca-2,5,8-triene into (3E,5Z,8Z)-2-acetoxydeca-3,5,8-triene and steps in syntheses leading to the natural products 9-hydroxyoctadeca-10,12-dienoic acid (α-dimorphecolic acid, obtained as its methyl ester) and (2E,4Z)-deca-2,4-dienal.Studies of a variety of substrates show that the order of reactivity of double bonds in the PdII-catalysed rearrangement is E-disubstituted > Z-disubstituted ca. vinyl > α-methylvinyl.Pd0-catalysed rearrangements of these substrates proceed, in contrast to the PdII-catalysed rearrangements, to thermodynamically controlled product(s), e.g. the above triene gives mainly (3E,5E,8Z)-2-acetoxydeca-3,5,8-triene.

Oxidation by Cobalt(III) Acetate. Part 10. Effects of Ring Substituents on the Product Distributions in the Oxidation of β-Methylstyrenes by Cobalt(III) Acetate in Acetic Acid

The oxidation of ring-substituted β-methylstyrenes by cobalt(III) acetate in acetic acid has been studied by product analysis and the relative rates were measured by a competition method.Electron-releasing groups (p-MeO, pMe and p-But) accelerated both the reaction rate and the formation of glycol monoacetates, while electron-withdrawing groups (p-Cl and m-Cl) not only retarded the reaction but also favoured the formation of allylic acetate instead of glycol monoacetate.The good relationship of relative rates with ?+ in the Hammett plot showed that both products were derived from the same intermediate.The reaction mechanism is discussed in connection with the stabilities of radical cations formed by a one-electron transfer from the olefins to cobalt(III) acetate.